Gmail and Outlook: AI to Sort Emails After Vacation

Google and Microsoft's messaging services can now summarize threads, retrieve information on demand, and sort your emails using natural language instructions. However, these features are not available everywhere or for all accounts. Here's an overview of access, usage, and settings to save time upon returning from vacation.

Access and Restrictions: Licenses, Regions, and Account Types

At Microsoft, conversation summarization and questions about the inbox or calendar are accessible to any Microsoft 365 business or educational account without needing an additional Copilot license. However, sorting emails using natural language via Copilot Chat is reserved for business or educational accounts with a Microsoft 365 Business or Enterprise subscription and an additional Copilot license; it is not included in consumer offerings. On the Gmail side, automatic summarization is disabled by default for users located in the EEA, the UK, Switzerland, and Japan, regardless of account type. Conversational search in Gmail is only available to Google AI Pro and Google AI Ultra subscribers. The "Help me write" feature also varies by profile: it is not offered in France on a free personal Google account, remains limited to users in the United States, and requires writing in English to customize the tone; on a paid Google Workspace or Google AI account, it is available in France and supports multiple languages. Queries like "Which emails received during my vacation require a response this week?" only work with a Google AI Pro or Ultra subscription.

Summarizing Conversations: Above the Thread in Gmail, in a Pane in Outlook

Gmail produces an AI-generated overview that condenses the key points of a long exchange and displays it above the conversation. This option, available on all accounts worldwide including free accounts when activated, automatically appears on sufficiently long threads; it can also be generated on demand via the "Summarize this email" button. The summary can be collapsed or expanded at will and remains visible as long as the thread is open. In Outlook, Copilot extracts important elements from a thread either directly in the conversation view or in a side pane depending on the version. The summary covers all messages in the thread, with references—sometimes numbered—to each cited email.

Searching and Sorting in Natural Language: Subscriptions Required Depending on Platforms

Gmail's conversational search allows direct questions in the inbox to retrieve a quote or check a deadline; it is reserved for Google AI Pro and Ultra offerings. A query in French like "Which emails received during my vacation require a response from me this week?" is among the features offered to help find the thread, but this option is only accessible to holders of these subscriptions. In Outlook, the Copilot Chat pane, accessible by clicking on the corresponding icon, allows users to give instructions to pin, archive, mark as read or unread, and generate automatic sorting rules. However, these features only apply to business or educational accounts associated with Microsoft 365 Business or Enterprise and possessing an additional Copilot license; they are not included in plans aimed at the general public. Finally, it is worth noting that Slack offers AI options to summarize a channel, initiate searches in natural language, and translate messages.

Drafting and Sending: "Help Me Write" and the Claude Connector

Gmail's "Help me write" feature, which became free for everyone in January 2026, can generate a draft from a prompt or rework a text to modify its tone or length. Access varies by account: it is not available in France on a free personal Google account, remains limited to users in the United States, and requires a draft written in English for tone customization; holders of a paid Google Workspace or Google AI account have access in France, with support for multiple languages. Outside the Gmail interface, the Google Workspace connector for Claude already allowed users to check the inbox and draft emails from a conversation; it now also supports sending, replying to, and forwarding emails. By default, validation is required before each of these actions; with a Team or Enterprise plan, the organization owner can disable this step for all members.

Activating and Configuring: Steps in Gmail and Display Conditions in Outlook

To activate summarization in Gmail, you need to open the settings and then "See all settings." In the General tab, scroll down to "Smart features" and check "Enable smart features in Gmail, Chat, and Meet." Still in General, you should access "Manage smart features settings for Workspace," enable "Google Workspace smart features," and then confirm the registration. In Outlook, the summary appears after selecting "Summarize this email" at the top of the thread; for Copilot to group conversations appropriately, it is necessary to enable conversation view; otherwise, each email will remain independent, and no thread will be synthesized. Google officially announced at the beginning of January 2026 the integration of Gemini into Gmail with five new AI features; on Microsoft's side, Copilot in Outlook supports several specific functions for sorting and drafting.